Synthetic Route of 159847-83-3, The chemical industry reduces the impact on the environment during synthesis 159847-83-3, name is Methyl 2-amino-4-cyanobenzoate, I believe this compound will play a more active role in future production and life.
To a solution of 7-ethoxy-2,3-dihydro-2,2-dimethyl-a-(1-methylethyl)-5-benzofuranmethanol (11.3 g, 42.9 mmol) and methyl 2-amino-4-cyanobenzoate (6.30 g, 35.8 mmol) in toluene (40 ml) and acetic acid (25 ml) was added conc. sulfuric acid (5.92 ml, 111 mmol) under ice-cooling, and the mixture was stirred for 2 hours at 80C. Methanol (18 ml) was added dropwise thereto, and the mixture was stirred for 30 minutes at 65C. After cooling, the reaction mixture was combined with ice water, neutralized with sodium hydrogen carbonate, and extracted three times with ethyl acetate. The combined organic layer was extracted three times with 1 M hydrochloric acid, and the combined aqueous layer was neutralized with sodium hydrogen carbonate, and extracted twice with ethyl acetate. The combined organic layer was washed with a saturated aqueous solution of sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure. To the residue was added ethyl acetate, and the precipitated crystals were removed. The mother liquor was concentrated under reduced pressure, and the residue was purified with a basic silica gel column chromatography (hexane/ethyl acetate, 5:1 followed by 3:1) to give the title compound (7.33 g, yield 49%). Amorphous. 1H NMR (CDCl3) delta 1.24 (6H, s), 1.33 (6H, s), 1.46 (3H, t, J = 7.0 Hz), 2.36 (2H, s), 2.66 (2H, s), 3.89 (3H, s), 4.18 (2H, q, J = 7.0 Hz), 5.76 (2H, s), 6.59 (1H, s), 6.62 (1H, dd, J = 7.8, 1.5 Hz), 6.73 (1H, d, J = 1.5 Hz), 7.85 (1H, d, J = 7.8 Hz).
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-amino-4-cyanobenzoate, other downstream synthetic routes, hurry up and to see.